Applications of polymer-bound phosphitylating reagents in the synthesis of organophosphorus compounds

ORGN 240

Yousef Ahmadibeni, yahmadibeni@mail.uri.edu, Michael Hanley, mhanley21@gmail.com, Hitesh Kumar Agarwal, hkag@rediffmail.com, and Keykavous Parang, kparang@uri.edu. Department of Biomedical and Pharmaceutical Sciences, University of Rhode Island, 41 Lower College Road, University of Rhode Island, Kingston, RI 02881
Ready access to organophosphorus compounds is an important requirement for studying several fundamental biological processes and pathways. A limited number of chemical strategies have been developed for the synthesis of organophosphorus compounds. To facilitate the synthesis of diverse and novel organophosphorus derivatives, we developed a number of solid-supported phosphitylating reagents that were used in the synthesis of nucleoside and/or carbohydrate phosphates, diphosphates, dithiophosphates, triphosphates, trithiophosphates, b-triphosphates, a,b or b,g-methylene-triphosphates, a,b-methylene-b-triphosphates, phosphodiesters, thiophosphodiesters, diphosphodiesters, triphosphodiesters, tetraphosphodiesters, and oligodeoxynucleotides containing diphosphodiester bridges. The solid-phase strategy offered several advantages. (i) Synthesis of a diverse number of compounds was made possible in a short time without the need to use protected nucleosides and carbohydrates. (ii) This strategy offered the advantage of facile isolation and the recovery of monosubstituted final products. (iii) This approach made use of the presence of reagents on a rigid solid support having a hindered structure, thereby allowing for the regioselective reactions.

 

Combinatorial and Process Chemistry
8:00 AM-11:40 AM, Monday, March 26, 2007 McCormick Place East -- Room E350, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007